I just upgraded the blog to Typo 5.2. I had a couple of issues, but things worked reasonably ok. Just in case this helps anyone, these are the issues I ran into:

I had to install a ridiculous amount of dependencies, sometimes to go from version 1.1.1 to 1.1.3 of some module. I really wonder if Typo 5.2 really needs those versions.

When trying to upgrade, it seemed to hang in this line: Backing up to /var/www/virtual/hcoder.org/db/backup/backup-20090223-1843.yml. It turns out, it didn’t really hang, it just takes a good while (and yeah, the file stays at 0 bytes for a long time too)

I had some permission issues that I had to fix (when upgrading, it tried to modify/copy some files, and it couldn’t)

When applying the migrations, it died with a really strange error message. It turns out, my version of Rubygems was too old ????

While writing this first post, I see some improvements in the admin interface, although I still can’t see any kind of “preview”. I hope it helps me with my struggle with spam, at least :-/